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inquiryProduct description: Product name Bromopentafluorobenzene CAS number 344-04-7 Assay ≥98% Appearance Colorless liquid Capacity 200mt/year Application Pharmaceutical/Pesticide/
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Name Bromopentafluorobenzene CAS NO. 344-04-7 Molecular Formula C6BrF5 Molecular Weight 246.96 EINECS 206-449-0
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Cas:344-04-7
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Cas:344-04-7
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inquiryBromopentafluorobenzene CAS:344-04-7 Specification Product name Bromopentafluorobenzene CAS number 344-04-7 Assay ≥98% Appearance Colorless liquid Capacity 200mt/year Applic
Cas:344-04-7
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inquirybromopentafluorobenzene
Conditions | Yield |
---|---|
With bromine In diethylene glycol dimethyl ether at 10℃; for 0.0833333h; | 100% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; boron trifluoride at 20℃; for 1h; | 96% |
With tris(pentafluorophenyl)borate; bromine; chlorine In chloroform at 30 - 35℃; for 2h; Reagent/catalyst; Solvent; Temperature; Large scale; | 93% |
With aluminum (III) chloride; bromine at 45℃; for 18h; | 90.5% |
Conditions | Yield |
---|---|
With bromine; cesium fluoride In acetonitrile at 20℃; for 3h; | 93% |
2,3,5,6-tetrafluorothiophenol
A
1-bromo-2,3,5,6-tetrafluorobenzene
B
bromopentafluorobenzene
Conditions | Yield |
---|---|
With bromine at 500 - 510℃; | A 87% B n/a |
Conditions | Yield |
---|---|
Stage #1: Hexafluorobenzene With iron(III)-acetylacetonate; ethylmagnesium bromide In tetrahydrofuran at -30℃; for 1.5h; Stage #2: With bromine In tetrahydrofuran at -30 - 20℃; | 83% |
Conditions | Yield |
---|---|
In diethyl ether reaction at 20°C, 1 hour;; | 69% |
In diethyl ether reaction at 20°C, 1 hour;; | 69% |
Conditions | Yield |
---|---|
With bromine at 500℃; | 68% |
Conditions | Yield |
---|---|
at 100°C in HBr; | 63% |
at 100°C in HBr; | 63% |
Pentafluorobenzene
A
bromopentafluorobenzene
B
3-H-pentafluoro-2,5-cyclohexadien-1-one
C
1,2,3,3,4,6,6-heptafluorocyclohexa-1,4-diene
Conditions | Yield |
---|---|
With bromine trifluoride; antimony pentafluoride In fluorosulfonylchloride at -90 - -80℃; for 0.5h; | A 57% B 13% C 9% |
Pentafluorobenzene
A
bromopentafluorobenzene
C
1-bromoheptafluoro-1,4-cyclohexadiene
Conditions | Yield |
---|---|
With bromine trifluoride; boron trifluoride In fluorosulfonylchloride at -90 - -80℃; for 0.333333h; Title compound not separated from byproducts; | A 47% B 10 % Chromat. C 10 % Chromat. |
With bromine trifluoride; boron trifluoride In fluorosulfonylchloride at -90 - -80℃; for 0.333333h; | A 47 % Chromat. B 10% C 10 % Chromat. |
Pentafluorobenzene
A
bromopentafluorobenzene
B
3-H-pentafluoro-2,5-cyclohexadien-1-one
C
2,3,3,4,5,6,6-heptafluoro-1-bromo-cyclohexa-1,4-diene
Conditions | Yield |
---|---|
With bromine trifluoride; boron trifluoride In fluorosulfonylchloride at -90 - -80℃; for 0.333333h; | A 46% B 26% C 10% |
A
bromopentafluorobenzene
B
2,3,3,4,5,6,6-heptafluoro-1-bromo-cyclohexa-1,4-diene
C
1-bromo nonafluoro cyclohexene
Conditions | Yield |
---|---|
With bromine trifluoride; hydrogen fluoride at -40 - -30℃; Inert atmosphere; | A 0.1 mmol B 0.16 mmol C 0.06 mmol D 45% |
perfluoropropylene
pentafluorophenyl lithium
A
bromopentafluorobenzene
B
cis-1-perfluoro(phenylpropylene)
C
trans-1-perfluoro(phenylpropylene)
Conditions | Yield |
---|---|
In diethyl ether byproducts: trans-perfluoro(α-(4-biphenyl)propylene); stream of dry argon between -80 and 50°C, keeping the mixt. at -70°Cfor 3 h, then acidifying with 10 % HCl at 10°C; | A 5% B 8% C 40% |
In diethyl ether |
Pentafluorobenzene
A
bromopentafluorobenzene
B
3-H-pentafluoro-2,5-cyclohexadien-1-one
C
1,2,3,3,4,6,6-heptafluorocyclohexa-1,4-diene
D
2,3,3,4,5,6,6-heptafluoro-1-bromo-cyclohexa-1,4-diene
Conditions | Yield |
---|---|
With bromine trifluoride; antimony pentafluoride In fluorosulfonylchloride at -90 - -80℃; for 0.5h; | A 35% B 1% C 26% D 17% |
pentafluorophenyl hydrazine
A
2,3,4,5,6-pentafluoroaniline
B
bromopentafluorobenzene
Conditions | Yield |
---|---|
With bromine In ethanol with ethanolic Br2 soln. at -60°C (2 h); | A 5% B 24% |
With Br2 In ethanol with ethanolic Br2 soln. at -60°C (2 h); | A 5% B 24% |
tribromofluoromethane
A
Hexafluorobenzene
B
1,2-difluorotetrabromoethane
C
bromopentafluorobenzene
Conditions | Yield |
---|---|
at 630 - 640℃; |
chloro-trimethyl-silane
pentafluorphenylbrom(V)tetrafluorid
A
trimethylsilyl fluoride
B
bromopentafluorobenzene
Conditions | Yield |
---|---|
In acetonitrile |
2,3,4,5,6-pentafluoroaniline
A
bromopentafluorobenzene
B
Pentafluorobenzene
Conditions | Yield |
---|---|
With copper(I) bromide; sulfuric acid; copper(II) sulfate; potassium bromide; sodium nitrite; tetrakis[3,5-bis(trifluoromethyl)phenyl]borate anion 1) 0 deg C, dichloromethane, water 2) dichloromethane, water, 100 min, rt.; Yield given. Multistep reaction. Yields of byproduct given; | |
With copper(I) bromide; sulfuric acid; copper(II) sulfate; potassium bromide; sodium nitrite; tetrakis[3,5-bis(trifluoromethyl)phenyl]borate anion 1) 0 deg C, dichloromethane, water, 2) dichloromethane, water, 100 min, rt.; Yield given. Multistep reaction. Yields of byproduct given; |
trimethyl(pentafluorophenyl)silane
A
bromopentafluorobenzene
B
Pentafluorobenzene
C
decafluorobiphenyl
Conditions | Yield |
---|---|
With xenon difluoride; Bromoform; cesium fluoride In acetonitrile at 20 - 25℃; for 0.5h; | A 25 % Chromat. B 14 % Chromat. C 1 % Chromat. |
With xenon difluoride; Bromoform; cesium fluoride prototype reaction (oth. aryltrimethylsilanes); |
pentafluorphenylbrom(V)tetrafluorid
triphenylphosphine
A
bromopentafluorobenzene
B
triphenyldifluorophosphorane
Conditions | Yield |
---|---|
In acetonitrile at 0℃; |
pentafluorphenylbrom(V)tetrafluorid
tris(pentafluorophenyl)phosphine
A
bromopentafluorobenzene
B
difluorotris(pentafluorphenyl)phosphorane
Conditions | Yield |
---|---|
In acetonitrile at 0℃; |
Conditions | Yield |
---|---|
With bromine In gaseous matrix at 40℃; Thermodynamic data; collision energy E(c); |
Conditions | Yield |
---|---|
With aluminum tri-bromide; bromine at -20℃; for 76h; | |
Multi-step reaction with 2 steps 1: 76 percent / acetonitrile / 0.25 h / Ambient temperature 2: 100 percent / Br2 / bis-(2-methoxy-ethyl) ether / 0.08 h / 10 °C View Scheme |
Conditions | Yield |
---|---|
With bromine for 240h; Product distribution; Ambient temperature; |
Conditions | Yield |
---|---|
With xenon difluoride; hydrogen fluoride for 0.416667h; Ambient temperature; Title compound not separated from byproducts; | A 2 % Spectr. B 29 % Spectr. C 11 % Spectr. |
iodotrifluoromethane
A
trifluoromethyl radical
B
bromopentafluorobenzene
C
trifluoro-iodo-methane radical anion
Conditions | Yield |
---|---|
In gas at 36.9℃; Rate constant; |
trimethyl(pentafluorophenyl)silane
A
trimethylsilyl bromide
B
bromopentafluorobenzene
Conditions | Yield |
---|---|
With aluminum tri-bromide; bromine -20 deg C -> rt., 15 min; Yield given; |
di-(pentafluoro phenyl) dimethyl silane
A
dimethyldibromosilane
B
bromopentafluorobenzene
Conditions | Yield |
---|---|
With aluminum tri-bromide; bromine Ambient temperature; -20 deg C -> r.t., 15 min; Yield given; |
di-(pentafluoro phenyl) dimethyl silane
A
bromopentafluorobenzene
B
Pentafluorobenzene
C
Brom-dimethyl-pentafluorphenyl-silan
Conditions | Yield |
---|---|
With aluminum tri-bromide In various solvent(s) for 0.5h; Ambient temperature; Yield given. Yields of byproduct given; |
pyridine
dichloro(ethylenediamine)platinum(II)
bromopentafluorobenzene
[N,N'-bis(4-bromo-2,3,5,6-tetrafluorophenyl)ethane-1,2-diaminato]dipyridineplatinum(II)
B
carbon dioxide
Conditions | Yield |
---|---|
With Tl2CO3 In pyridine N2-atmosphere; stirring (115°C, 1 h); evapn. (vac.), light petroleum addn., stirring (1 h), decanting, extg. (Me2CO), filtering, concg., light petroleum addn., crystn. on concg., re crystn. (Me2CO / light petroleum); | A 60% B 100% |
With K2CO3 In pyridine N2-atmosphere; stirring (115°C, 1 h); evapn. (vac.), light petroleum addn., stirring (1 h), decanting, extg. (Me2CO), filtering, concg., light petroleum addn., crystn. on concg., re crystn. (Me2CO / light petroleum); | A 26% B 30% |
Conditions | Yield |
---|---|
With n-butyllithium; carbon dioxide; boron trichloride In hexane; water; pentane | 99% |
bromopentafluorobenzene
diethylmagnesium
bis-(pentafluoro phenyl) magnesium
Conditions | Yield |
---|---|
In tetrahydrofuran reaction at 0°C;; | 99% |
tetrahydrofuran
indium
bromopentafluorobenzene
bromine
bis(tetrahydrofuran)(pentafluorophenyl)indium dibromide
Conditions | Yield |
---|---|
In tetrahydrofuran | 99% |
Conditions | Yield |
---|---|
In dichloromethane | 99% |
Conditions | Yield |
---|---|
In dichloromethane elem. anal.; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1-cyclobutyl-1-phenyl-methanone With sodium hexamethyldisilazane In tetrahydrofuran; 1,4-dioxane for 0.0833333h; Inert atmosphere; Stage #2: bromopentafluorobenzene In tetrahydrofuran; 1,4-dioxane for 0.25h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
In diethyl ether at 20℃; for 3h; Inert atmosphere; | 99% |
bromopentafluorobenzene
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In tetrahydrofuran for 18h; Inert atmosphere; Reflux; | 99% |
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In tetrahydrofuran at 80℃; for 18h; |
styrene
bromopentafluorobenzene
(E)-1,2,3,4,5-pentafluoro-6-styrylbenzene
Conditions | Yield |
---|---|
With (NBu4)2[Pd2(μ-Br)2(C6F5)2Br2]; calcium carbonate In 1-methyl-pyrrolidin-2-one; water at 130℃; for 24h; Heck reaction; | 98% |
With 1,3-bis(2-(diphenylphosphinomethyl)-phenyl)benzene*PdCl2; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 25h; Heck coupling; | 67 % Chromat. |
bromopentafluorobenzene
ethylmagnesium bromide
2,3,4,5,6-pentafluorophenylmagnesium bromide
Conditions | Yield |
---|---|
In tetrahydrofuran reaction at 0°C;; | 98% |
In diethyl ether | |
In di-isopropyl ether |
Conditions | Yield |
---|---|
With magnesium In diethyl ether Ar-atmosphere; addn. of 1 equiv. of SnCl4 to tetraallyltin at -50°C, warming to 0°C, dropwise addn. of excess of Grignard reagent (prepd. from Mg and C6F5Br), stirring (room temp., 38-75 h); filtration (celite), chromy. (SiO2, hexane), evapn., chromy. (SiO2, hexane); elem. anal.; | 98% |
tetrahydrofuran
bromopentafluorobenzene
bis(tetrahydrofuran)(pentafluorophenyl)indium dibromide
Conditions | Yield |
---|---|
In tetrahydrofuran InBr suspended in THF, C6F5Br added, stirred for 16 h at ambient temp.; volatile distilled off in vac. at ambient temp.; elem. anal.; | 98% |
bromopentafluorobenzene
1,1,3,3-tetramethylbutane isonitrile
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
N-[(2-bromophenyl)(pentafluorophenyl)methylene]-tert-octylamine
Conditions | Yield |
---|---|
With potassium fluoride; 18-crown-6 ether In 1,2-dimethoxyethane at 0℃; for 14h; Inert atmosphere; regioselective reaction; | 98% |
bromopentafluorobenzene
A
cyclopentadienyl iron(II) dicarbonyl dimer
B
p-HC6F4Fe(CO)2Cp
Conditions | Yield |
---|---|
With (C6H5)(C2H5)CHCN In tetrahydrofuran byproducts: C6F5H; at room temp. using Ph(Et)CHCN as radical trap; not isolated, detected by NMR; | A 97% B 3% |
pyridine
cis-(N,N-dimethyl-ethylenediamine)diiodoplatinum(II)
thallous 2,3,5,6-tetrafluorobenzoate
bromopentafluorobenzene
c(N),d(N')-{N,N-dimethyl-N'-(4-bromo-2,3,5,6-tetrafluorophenyl)ethane-1,2-diaminato(1-)}-b-iodo-a-pyridineplatinum(II)
B
carbon dioxide
Conditions | Yield |
---|---|
In pyridine Heating under stirring (105-110°C, N2, 25 min).; Cooling, evapn. to dryness (vacuum), washed (light petroleum), dried, extn. with Me2CO, filtn. of TlI, evapn. to dryness, washed (cold EtOH), recrystn. (pyridine/H2O and ether/light petroleum), elem. anal.; | A 27% B 97% |
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran; diethyl ether Ar-atmosphere; mixing equimolar amts. of Mg and PhBr (in ether, 0°C), stirring for 2 h, dropwise addn. of Sn-compd. (in THF) to slight excess of Grignard reagent at 0°C, stirring (room temp., 63 h); filtration (celite), chromy. (SiO2, hexane), evapn., chromy. (SiO2, hexane); elem. anal.; | 97% |
bromopentafluorobenzene
trimethylsilylacetylene
((trimethylsilyl)ethynyl)pentafluorobenzene
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In toluene at 80℃; for 19h; Inert atmosphere; | 96% |
With bis(benzonitrile)palladium(II) dichloride; copper diacetate; diisopropylamine; triphenylphosphine 1.) RT, 1 h, 2.) reflux, 1 h; | 20% |
With copper(l) iodide; diisopropylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride | |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine at 72℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere; |
Conditions | Yield |
---|---|
With [Pd(η2-dibenzylideneacetone)(tris(o-tolyl)phosphine)2]; potassium carbonate In ethanol; water; toluene at 85℃; Suzuki-Miyaura Coupling; Inert atmosphere; | 96% |
With bis(trisphenylphosphine)(dibenzylideneacetone)palladium(0); sodium carbonate In ethanol; toluene at 60 - 90℃; for 2 - 20h; Reagent/catalyst; Temperature; Time; Suzuki-Miyaura Coupling; | 92% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene Heating; |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -30℃; Temperature; Flow reactor; | 95.2% |
Stage #1: bromopentafluorobenzene With ethylmagnesium bromide In octamethylcyclotetrasiloxane at 20℃; for 0.00972222h; Inert atmosphere; Stage #2: Trimethyl borate In octamethylcyclotetrasiloxane at 10℃; for 0.0138889h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere; | 94.5% |
With magnesium In diethyl ether Grignard-comp. prepd. from Br-compd. and Mg in ether was cooled with ice-water bath and added dropwise to 1.5 equiv. of pre-cooled (ice-water bath) soln. of B(OMe)3 in ether, stirring at 0-4 °C for 1 h; pouring into 5 % HCl, org. layer was sepd., aq. layer was extd. with ether, extracts were combined, dried with MgSO4, evapd. under vac., solid was recrystd. from hot toluene, elem. anal.; | 90% |
Stage #1: bromopentafluorobenzene With magnesium In tetrahydrofuran at 40 - 45℃; for 5h; Inert atmosphere; Large scale; Stage #2: Trimethyl borate In tetrahydrofuran at -5℃; for 2h; Inert atmosphere; Large scale; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.5h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Large scale; | 90.33% |
bromopentafluorobenzene
antimony(III) chloride
tris(pentafluorophenyl)antimony
Conditions | Yield |
---|---|
Stage #1: bromopentafluorobenzene With n-butyllithium at -78℃; for 0.25h; Stage #2: antimony(III) chloride at -78 - 20℃; for 2h; | 95% |
With magnesium In diethyl ether at -10 - 20℃; for 2h; Heating / reflux; | 65% |
bromopentafluorobenzene
dimethyltin dichloride
dimethylbis(pentafluorophenyl)tin
Conditions | Yield |
---|---|
With BuLi; H2O In diethyl ether; hexane Ar-atmosphere; stirring (-78°C, 45 min), Sn-compd. addn., stirring (-78°C, 15 min, room temp., 12 h), wet hexanes addn.; evapn. (reduced pressure), extg. (hexanes), evapn., distg. (reduced pressure); | 95% |
Stage #1: bromopentafluorobenzene With iodine; magnesium In diethyl ether for 4h; Heating / reflux; Stage #2: dimethyltin dichloride In diethyl ether at 0 - 20℃; | 90% |
bromopentafluorobenzene
boron trifluoride diethyl etherate
tris(pentafluorophenyl)borate
Conditions | Yield |
---|---|
Stage #1: bromopentafluorobenzene With magnesium In diethyl ether at 20℃; Stage #2: boron trifluoride diethyl etherate In toluene at 0℃; for 1h; Schlenk technique; Inert atmosphere; Stage #3: In diethyl ether; toluene at 100℃; for 1h; Schlenk technique; Inert atmosphere; | 95% |
Stage #1: bromopentafluorobenzene With magnesium In diethyl ether for 1h; Reflux; Stage #2: boron trifluoride diethyl etherate In toluene at 100℃; for 1h; | 88% |
Stage #1: bromopentafluorobenzene With magnesium In diethyl ether at 20℃; for 1h; Inert atmosphere; Stage #2: boron trifluoride diethyl etherate In toluene at 100℃; for 1h; Inert atmosphere; | 88% |
bromopentafluorobenzene
1-(4-vinylbenzyl)-1H-imidazole
Conditions | Yield |
---|---|
In acetonitrile at 60℃; for 2h; Inert atmosphere; | 95% |
bromopentafluorobenzene
naphthalene-2-boronic acid
2-(2,3,4,5,6-pentafluorophenyl)naphthalene
Conditions | Yield |
---|---|
With potassium phosphate tribasic trihydrate; palladium diacetate; tricyclohexylphosphine In water; toluene for 12h; Inert atmosphere; Reflux; | 95% |
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 2h; Inert atmosphere; | 94.3% |
With n-butyllithium In hexane; Petroleum ether at -78℃; for 1h; | |
With p-tolyllithium In tetrahydrofuran at -70 - -55℃; for 1h; |
bromopentafluorobenzene
4,4'-Difluorobenzophenone
2,3,4,4',4'',5,6-heptafluoro-triphenylmethanol
Conditions | Yield |
---|---|
Stage #1: bromopentafluorobenzene With magnesium In diethyl ether Metallation; Stage #2: 4,4'-Difluorobenzophenone In diethyl ether for 3h; Grignard reaction; Heating; | 94% |
bromopentafluorobenzene
1,1-bis(pentafluorophenyl)-2,4-bis(2,4,6-tri-tert-butylphenyl)-1,3-diphospha-2,4-diazene
Conditions | Yield |
---|---|
Stage #1: bromopentafluorobenzene With n-butyllithium In diethyl ether at -80℃; for 0.25h; Stage #2: N-(2,4,6-tri-tert-butylphenyl)-N-trimethylsilylamino(dichloro)phosphane In diethyl ether at -80℃; | 93.4% |
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